Woodstock Inn, VT Wedding Photographer :: Simon Pearce Proposal :: Trevor + Alison

Warning: I was so excited about this shoot that I've written somewhat of an epic essay. If you can't be bothered to read my ramblings then here's the short version. Once upon a time, a boy named Trevor asked a girl named Alison to marry him. Alison said yes. I photographed them. The End.

But if you're not in a rush you should grab a drink and settle in....

Over the last five years I've photographed a LOT of engagement pictures and I often ask the couples about the proposal story. They frequently show me a blurry little picture on their cell phone taken moments after they got engaged and I've always wanted to photograph an actual proposal. Other than the time I sort of crashed a Boston proposal **here**, it just doesn't seem to come up.

So imagine my delight when I got this email from Trevor in February:
"I'm trying to find a great professional photographer to take engagement photos in Woodstock, Vermont . This is for a surprise engagement that would happen earlier in the day"

I was ALL OVER this :) For about a month Trevor and I emailed back and forth and came up with a genius plan for paparazzi style proposal photography at the Woodstock Inn where Trevor was planning to ask Alison to be his wife. Trevor had a master plan about the whole proposal itself but more on that in a little bit. That sunny Wednesday in March came around really quickly and I drove up to Woodstock, VT with the awesome Lena from Hair That Moves who Trevor had hired to surprise Alison with professional hair and make up!

Lena and I were SO excited on the drive up, we had all sorts of "what if...?" conversations:
- What if I don't recognise them and miss the proposal?
- Trevor and Alison were flying to New England. What if Alison decides to fly in sweats? [Unlike me, Alison was a very stylish flyer]
- What if Alison just wants to relax and refuses to take a walk with Trevor? [I think this was the closest the plan came to derailing but luckily the unseasonably warm sunshine was tempting enough]
- What if Alison says no?!!? [We didn't really think this one was a possibility but still...]

We arrived at the beautiful quaint Woodstock Inn in Woodstock, VT (where I had taken wedding pictures last November) and pretended to be casually hanging out in the lobby whilst secretly checking everyone out who entered the Inn. Finally Trevor and Alison arrived and we easily recognized them from the picture Trevor had emailed. Lena and I were like master spies engaging in our pre-determined fake conversation "Did you hear about that new Italian restaurant? Should we try it for dinner?" so as not to arouse any suspicion from Alison. Trevor gave me a very subtle nod and the plan was GO!!!

Of course, any well-prepared plan can easily go awry and the initial proposal location had to be nixed due to rather ugly looking black plastic sheeting protecting the hedges through the winter. A couple of sneaky text messages later we figured the gardens at the back of the inn would work. The only issue was that the only possible hiding place for me was a very small Christmas tree. On a slope. Of stone and dirt. So I precariously scrambled down the slope, got a good footing in the dirt and waited...

...and everything went perfectly!!!

What's that? You'd like to see the ring that's causing Alison's expression? Okay then...

Trevor and Alison headed back to the inn; Alison still completely unaware that the whole proposal had been photographed :) I climbed up the dirt slope, brushed the leaves from my clothes, Lena snuck out of the door she'd been behind and the two of us were all "Squeeeee! She said yes!! Wasn't it adorable!!!" and then it was on to part II of Trevor's master plan.

Alison and Trevor were excitedly calling friends and family to tell them the happy news when Lena and I arrived to say "Hello!!! We're here to do professional hair and make up and then we're taking engagement pictures before your dinner reservation!!!" Alison was all "What?!!?" It was awesome! I'd originally hoped to be able to sneak to the local drugstore to get a print of one of the proposal pictures but wouldn't you know it - Woodstock's only one-hour photo lab wasn't operating :( Luckily the front desk team of the Woodstock Inn were FABULOUS! I downloaded a file to my laptop, quickly edited it, inserted it in a word document and they printed it at the front desk. Obviously not a professional print but it was such a happy moment that I figured Trevor and Alison would be good with it :)

Here's Alison excitedly calling everyone in her contact list whilst Lena does her usual hair and make up magic:

We then took a little walk around Woodstock for engagement pictures stopping at the covered bridge:

Trevor and Alison met through a mutual friend and had their first date at a Simon Pearce restaurant that has since closed. Trevor knew there was another Simon Pearce restaurant in Quechee, VT hence his master plan to fly Alison there for the proposal and dinner! What a guy!!!

Did I mention the limo that Trevor hired? Filled with flowers. And a happy newly engaged couple:

Simon Pearce is not only a favorite Vermont wedding venue, it's also the perfect location to celebrate your engagement:

You think the restaurant looks kind of quiet? Well maybe that's because Trevor rented out the WHOLE ROOM. Um hum. And he'd worked with Tedd Kapinos of Jasper & Prudence Floral and Events to have the room filled with beautiful yellow roses and sunflowers and candles...

It was at that point Lena and I said our goodbyes and left a very happy Trevor and Alison to enjoy their evening together. We got this lovely email from Trevor the day they arrived home:
"I wanted to thank both of you for helping me make Alison's night perfect! I appreciate everything you both did and all of the assistance you gave me along the way! Thank you again very much. I couldn't have imagined it going any better and couldn't have planned a night like that without either of you!"
Trevor is being too kind. As Lena and I said on the day "Alison! You've got a keeper!!!" Trevor put a huge amount of thought and effort into everything - the hotel, the limo, the flowers, the restaurant, hair, make up, photographs...but I think the most memorable part of the day was seeing just how incredibly happy these two were to know they'll be spending the rest of their lives together. Best post-proposal hug ever:

Oh go on then, seeing as it's Friday afternoon. One more picture - this might be my favorite:

Hugest congratulations to Trevor & Alison. Thank you SO much for trusting me to photograph this momentous moment in your lives! I am so happy you can share it with your friends and family though these proposal photographs!


  1. Congratulations to Trevor and Alison!

    Leah! I'm so excited to see all these photos...been waiting since the preview. :) They are amazing! So glad you got to photograph their proposal. Professional photographs make a world of difference!

    :) Meg

  2. Oh my goodness LOVE LOVE LOVE! The last picture is definitely my favorite but the whole story is beautifully photographed and written. What a lucky girl!!!

  3. Over a year later and I love these pictures even more than I did then! Trev and I are doing well and looking forward to our big day. Thank you again Leah and Lena! I just LOVE reading this over and over and I can't imagine better pictures!!!